A packaging machine is often used to package an item for shipping. A packaging machine can package the item in a suitable enclosure, such as an envelope, bubble wrapping, or box. Some packaging machines require items to be supplied to the packaging machine in a particular orientation for packaging. For example, bubble mailer and envelope style packaging machines may require thin items to be supplied to the packing machine in a vertical orientation for proper packaging. Additionally, automated systems for feeding packaging machines increase throughput and efficiency as compared to manual feeding of items to packaging machines.